What risk(s) would you take if you knew for certain it would all work out?

and how do you define work out?

Two weeks ago, I asked on Instagram: What risks would you take if you knew it would all work out? And of course, before I could begin the next slide, I had a few write that “how is it deemed a risk if you know it will work out?” Sure, I get that. The question was nuanced, as is most of life. The next slide read: “And how do you define work out?”

Interesting thing here, I want to share:

Individuals responses to what they would deem “working out” could be broadly classified in to three categories. I’ve ranked them from most to least:

#1: Hard Numbers

“$300k annually and $3mm in the bank” - The majority gave hard numbers, and the hard numbers fell heavily in this bucket. This was an oddly agreed upon number here. Not that the number is odd, it makes sense, but I was surprised at such a general consensus amongst people who for the most part have never met.

#2: An Absence rather than a Presence

“Not to be in fear….” “Not to be hungry…..” “Not to be anxious and sad…..“. No feeling of regret….” It was interesting to me the preponderance of what we hoped for framed in a negative. The antonyms to all of this are to be safe, full, happy and proud. I found the particularly interesting as someone who reads my DM’s every day and find them rarely every tinged with anger, yet not overly Pollyanna either. Quite balanced and pragmatic. But in my mind, I associate that often with looking for something good rather than avoidance of something bad.

#3: Confirmation of $$$ or Business Stature maintenance

“Knowing that I won’t lose traction….” “Maintaining what I have……” This was framed in terms of dollars or career milestones. Someone who had reached a certain level in their career wanting some assurance that the opportunities would exist in other places. Or the dollars gained, the resulting lifestyle and the bank balances kept stet. I found it interesting that this was positioned in terms of hard numbers and titles, rather than the general adjectives of what has been accrued: happiness because I have enough money to travel, the ability to make big decisions and take actions because of my level….

You may know from previous stacks here, I’m a big fan of drilling down to first principles. Finding the common denominator. However you want to phrase it, the idea is that you want to really focus on the “so what” of it all. The end destination or feeling you want to achieve. It’s why many of you find it maddingly fustrating, at first, when you tell me how you want something to fit, what you are specifically wanting to buy, and I keep asking “but why” until we get to the core. It can seem counterintuitive that “prinicples” are not specifics and that specificity is what often leads us astray.

Here’s something I just read, and I wonder how this plays into thoughts I’m tossing in my head. A recent article in The Atlantic, here, has an article detailing the demonstrative decline in Americans mobility - moving from state to state. Interesting data is presented that reveals a staggering drop off in peoples (willingess? desire? need?) to just pick up and move. The numbers, no matter how you look, are eye popping. It makes me think how my parents picked us up and moved us from Chicago to St. Simons Island Georgia when I was 8. The environment, the financial opportunity, etc. didn’t allow for the quality of life my parents wanted for us and them. They didn’t pursue a strategy to work with their companies/employer to strategize a plan for growth. And they refused to bifurcate their life as in: ok we slog it out in the shit for now and then it will be better after years and then we become happy. They just picked up and moved my sister and I to an island we’d never been to. And they were seeking togetherness. Which to them meant happy, an ability to come home when it’s light out, play sports, be healthy. This aligned with their principles - to live their lives as if it’s actually happening to you. Right now. Which of course, it was. For my parents, everything worked out. $3mm? Hardly. But I know for certain that had that dollar figure been laid out there, the path would not have been so easy. And by easy, I mean led by small steps that at each step felt right, and were sometimes wrong, but they knew the destination.

I wonder what’s keeping people from picking up and leaving their homes? As I read the Atlantic Article, I felt that many of my DMs answered the question a bit. The certainty we, many, desire and the false hope that is often provided that anything in life can be so certain.

So I’m curious, as the discourse continues here, what risks would you take if you knew it would all “work out”? And how do you define “work out”?